Stereoselective syntheses of (+/-)-komaroviquinone and (+/-)-faveline methyl ether through intramolecular Heck reaction

Sengupta, S., Drew, M.G.B., Mukhopadhyay, R., Achari, B. and Banerjee, A.K. (2005) Stereoselective syntheses of (+/-)-komaroviquinone and (+/-)-faveline methyl ether through intramolecular Heck reaction. Journal of Organic Chemistry, 70 (19). pp. 7694-7700. ISSN 0022-3263 doi: 10.1021/jo051082i

Abstract/Summary

An efficient, flexible, and stereoselective convergent route for constructing the trans-10-hydroxy1,1-dimethyloctahydrodibenzo[a,d]cyclohepten-7-ones (5a-c) was achieved via intramolecular Heck reaction. This strategy has been successfully implemented for the syntheses of (+/-)-komaroviquinone (3) through (+/-)-coulterone dimethyl ether (5c) and (+/-)-faveline methyl ether (1a).